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Galena's historic Main Street -- named "Best Main Street in the Midwest" by Midwest Living magazine and one of America's Best Main Streets by Fodor's -- curves past nearly 100 19th-century storefronts. Galena looks much as it did during the time of the Civil War, although now the historic red brick buildings are home to charming boutiques, art galleries and restaurants. Galena is also known for its cozy lodgings, with quaint bed and breakfasts dotting the picturesque hillsides surrounding the town.

The Lawlor family proudly offers tours and tastings of more than 40 award-winning wines at its Galena Cellars Vineyard & Winery. Take a vineyard tour, then kick back with a glass of wine on the veranda. Galena Cellars also has a tasting room on Main Street in Galena, housed in a beautiful brick 1840s grain storehouse with a shaded wine patio.

From kayaking and biking to scooter rentals, Fever River Outfitters has everything you need to add a little adventure to your Galena getaway. The staff here knows the area well and offers excursions that take care of every detail—whether you’re kayaking to an island picnic or taking a scooter to a vineyard for an afternoon wine tasting. Want to explore on your own? Simply rent or purchase outdoor gear and set off on your own adventure along the many biking paths, waterways and winding roads of this scenic part of northwest Illinois.

Indulge your decadence in the heart of historic downtown Galena. With well over 200 flavors of Swiss, German, French, Belgian, Venezuelan and domestic chocolates – Chocolate’ is the destination all chocolate lovers must experience.